Journal of Organic Chemistry p. 3728 - 3732 (1985)
Update date:2022-08-10
Topics:
Baeckstroem, Peter
Jacobsson, Ulla
Koutek, Bohumir
Norin, Torbjoern
UV irradiation of thymol (7) at 254 or 300 nm in trifluoromethanesulfonic acid affords ten products, eight of which have been isolated and characterized.Four competitive processes are suggested to be operating in the formation of the photoproducts: (i) regioselective type A rearrangement leading to umbellulone (8, about 10percent, (ii) formal C2->C3 migration by type A rearrangement and ring opening which affords the principal products, 3-isopropyl-5-methylphenol (12, 17percent), (iii) intermolecular transalkylation leading to diisopropylphenols 13-15 (17percent), and (iv) formation ofpiperitenone (10, 5percent) initiated by hydrogen abstraction.A mechanism for the formation of 10 is proposed.Both para- and ortho-protonated 7 are suggested to be involved in product formation.
View MoreChongqing KonAo Health Co.,Ltd
Contact:13687578375
Address:wuhan hubei china
Hangzhou Ocean Chemical Co., Ltd.
website:http://www.hzoceanchem.com
Contact:+86-571-88025872, 28272092, 28272096
Address:Room 623 ,Building No 1 , COFCO Radius Commercial Center Xiwen Road, Xiacheng District, Hangzhou, Zhejiang Province, China
KINHENG CHEMICAL(SHANGHAI)CO., LTD.
Contact:+8621-60490170
Address:Room401, No.28,Lane 189, Yangshupu Rd. Shanghai, China.
Suzhou CarbonWell Pharma-Tech Co., Ltd
Contact:Tel: + 86 (0)512-8898-1216; + 86-18606258602
Address:2358 Changan Road, Wujiang Scientific Innovation Park, Wujiang, Jiangsu Province, P. R. China 215200
Contact:410-273-7300; 800-221-3953
Address:4609 Richlynn Dr., PO Box 369, Belcamp, MD, 21017-0369, USA
Doi:10.1016/0022-328X(85)87294-6
(1985)Doi:10.1002/cmdc.201600128
(2016)Doi:10.1002/chem.201201153
(2012)Doi:10.1016/S0040-4039(03)00375-7
(2003)Doi:10.1021/jo00932a001
(1974)Doi:10.1021/ja00881a023
(1962)